


Back in Town

by MioFromSpace



Category: Gossip Girl
Genre: Chuck has a Sister, Implied/Referenced Self-Harm, Implied/Referenced Suicide, Work In Progress, bisexual Chuck Bass, questioning Jenny
Language: English
Status: In-Progress
Published: 2018-12-17
Updated: 2019-02-03
Packaged: 2019-09-18 08:28:18
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 3,815
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16991505
Author URL: https://archiveofourown.org/users/MioFromSpace/pseuds/MioFromSpace
Summary: Chuck's younger half-sister Alexandra Bass returns to New York after going through a hard time. Her father wants to keep his daughter ot of the tabloids and away from a certain gossip bloggers website and so his strict rules keep Alex from having a big comeback. But when she sneaks out to go to Blair Waldorf's Masquerade Party, smartly dressed in a tuxedo instead of a dress, she ends up on Gossip Girl's blog anyway.It's a good thing Alex can count on her best friend and soon to be step brother Eric van der Woodsen. Once her first little scandal is dealt with Alex is ready to jump head first into the social life of an Upper East Side girl as well as a budding romance with one Jenny Humphrey.





	1. Let's Go to a Ball

**Author's Note:**

> I watched the first season of Gossip Girl about 9 years ago. Now that I'm rewatching the show, I thought I might also revisit my old fanfiction. This is a story my sixteen year old self came up with that I'm now rewriting.  
> The main character of this fanfic is an OC, Alexandra Bass, Chuck's younger half sister. This might not be the best thought through story out here and some characters might be ooc. But I'm kind of attached to the story and I really like drama. So here we go!  
> I know that by the end of the show it was revealed who Gossip Girl is. But let’s pretend for the sake of this fanfic that Gossip Girl is still just a random voice from the off with no personal connection to any of the characters.

**Seen at Blair Waldorf’s Masquerade Ball:**  
**A mysterious prince and a secretive princess dancing. The wonder of a masked ball, everybody is talking about them but no one knows who’s hiding behind the masks. Do they even belong to the in crowd or did they snug into an upper east side party without invitation?**  
**Either way, they might have been the cutest couple at the party, since Queen B did not get her desired dance with her Prince Charming Nate.**

 

\- One week earlier -

“I just wish my father would let me go out sometimes. Chuck can do whatever he wants. But for me he has a whole bunch of stupid rules, keeping me locked up in the hotel,” Alex complained to Eric.  
“I know too well what you mean. There seems to be a double standard between our troubled older siblings and the way we are treated. Must be a ‘spent some time in a mental hospital’ label. Serena gets to go out every night, but mum is so overprotective when it comes to me.” Eric said.  
“I can’t believe I’m saying this, but I’m actually looking forward to going back to school soon. Everything is better than spending all of my time either at therapy or at home.”  
“What’s your family’s excuse for your time in therapy anyway? Do you also have an aunt Carol in Miami?”  
“No, I think my father still let’s people think I’m at boarding school. I think you and your family are the only people that know I’m back in New York, or that I even exist.”

  
Eric picked up his phone and opened Gossip Girl's website. A quick search revealed that there was not a single entry about Alexandra Bass on the blog.  
“At least Gossip Girl is not writing about you.”  
“Like I said, no one even remembers I exist. Mum and I moved away six years ago, when I was ten.”  
“I remember how we used to play as kids,” Eric said.  
“I remember how Blair Waldorf would play dress up with me, as if I was a little doll, not Chuck’s sister.”

Alex had to laugh at this memory. She had grown up on the upper east side, but she was not part of it anymore. After the divorce her mother had taken her to Europe. And after her mother's death Bart had sent Alex to a boarding school. All Alex had wanted at that time had been to come back home to New York to be with her family. But her father did not understand much of child rearing and Alex suspected that he also wanted to shield her fourteen year old self from the socialite life of rich Upper East Side kids. Chuck was certainly a hand full on his own, even with an amarda of Nannies and other staff parenting him. Bart must have thought that a private boarding school was the better place for a teenage girl with a father who didn’t have much time to take care of her.

  
“Do you know when you’ll go back to school yet?” Eric asked.  
“No, I keep bugging my father about it, but he thinks I’m not ready yet. I will have to repeat my sophomore year anyway, I missed too much while I was at the clinic.”  
“I really hope I won’t have to repeat and that mum will let me go back sooner rather than later. It already felt as if she kept me in treatment for ages.”  
“It was only two months for you wasn’t it?”  
“Two months that would have been way worse, if you hadn’t shown up.”

  
After several month in a psychiatric hospital in the countryside, where Alex had felt just as lonely and isolated as she did at boarding school but with the added bonus of getting therapy and medication, Alex had finally convinced her father that she was better and ready to come home. She knew she never wanted to go back to boarding school. So the compromise for her to come live in New York again was that she would continue councelling at the Ostroff center. She was not an inpatient there. But she had to visit the center three times a week for individual councelling as well as group therapy, where she had met Eric van der Woodsen and they had rekindled their childhood friendship.

  
Alex had thought that coming back to New York would make her instantly feel better, but she had been wrong. Thanks to her therapy she was in a better state of mind again, her depression was under control. But she once again started feeling isolated and furthermore bored out of her mind. She missed having a social life. But besides Eric and her own brother Chuck she did not get to see many people. She was not allowed to go out in the evening and even during the day her father preferred it if she went out with an adult by her side. Usually that adult was her nanny, even though Alex had turned sixteen a month ago and was sure she did not need a nanny anymore. Luckily Bart Bass was a busy man, and so Alex often found ways to sneak out on her own for a few hours.

  
“I did not beg my father to let me come back to New York to stay home every day. I want to go to Blair’s parties!” Alex complained once again. She had picked up the laptop from the couch table and started scrolling through gossip girls blog. “I actaully kind of wish Gossip Girl would write about me, that would at least mean I have a life.”

 

**Invitations for Blair Waldorf’s Masquerade Extravaganza went out today and so the big question is: who’s invited and who will have to stay home that night? We all know that this is a party we don’t want to miss!**

 

“Have you heard that Blair is giving a masked ball?” Alex asked looking up from the laptop.  
“I heard Serena talking about it,” Eric said.  
“We should totally go! It’s perfect, everyone will be wearing masks, so no one will recognize us and our parents will never find out.”  
“You know Blair’s parties aren’t really my thing and I’m not sure if I’m up for the buzz,” Eric explained.  
“Okay, then I’ll go alone. But you will cover for me, right?” Eric knew that if Alex set her mind to something there was no way of stopping her. She had been that way even as a child and he smiled at the realization that the many years in Europe had not changed her all that much.

  
“Sure,” he agreed. “What will you wear? Maybe you can borrow a dress from Serena.”  
“Does she have any fancy dresses with long sleeves?” Alex asked. Eric was right, she did not have anything to wear for the occasion. Of course she could just go out and buy a dress, but she wasn’t sure if she’d have a chance to go shopping on her own before the party.  
“If I want to go full on incognito, maybe you could borrow a tux from me.” Eric joked. But Alex liked the idea.  
“Do you think you have anything that will fit me?”  
“You’re a little smaller than me, but I’ve outgrown half the things in my closet anyway.”

  
He got up from the couch and went into his bedroom where he started roaming through the clothes in the closet. He had not worn most of the things in months. During his stay at the center there had not been any occassions to put on a suit. He had lived in t shirts and sweat pants for weeks, only putting on proper jeans when his mother came to visit.  
Eric handed Alex who had followed him into the bedroom a white shirt and continued looking for a pair of pants that might fit her. Alex took off her sweatshirt to try on the shirt.

  
“You’re gonna get changed here?” Eric asked.  
“Do you mind me getting changed in front of you?”  
Eric shook his head.  
“Me neither,” Alex said. She did not mind if people saw her in her underwear when she changed, but she always tried to hide her arms from others. But Eric was different, he knew all about her scars and Alex knew that he would not judge her.

  
The shirt fit nicely. If she wore a tight top instead of a bra it would be even better. The pants were a little two long, but Alex could easily hem them with just a few stitches. Finally Eric found a matching waistcoat and blazer.

  
Alex looked at herself in the mirror.  
“This is great, now I only need a mask.”


	2. Burning Glances, Turning Heads

**Summary for the Chapter:**

> At Blair's masquerade party Alex runs into Jenny who has just realised her revenge on Chuck.

Alex tied her hair into a low knot, put on the mask and finally the top hat. Looking at herself in the mirror she couldn’t help but think that she looked like Tuxedo Mask minus the cape. She wished she had a cape.

Sneaking out would be easy. Bart Bass was at the party that Eleanor Waldorf was hosting. All Alex had to do now was to take the back exit of the hotel, so the concierge would not see her. And she had to be back before her father came home.

Getting into the party was even easier. She arrived at the same time as Nate Archibald. As her brother’s best friend he was one of the few people who knew that she was back in the city. Alex simply revealed her identity to him and asked him if she could come in with him. Since he was noted on the guest list as a guest of honor, there was no problem when he asked the doorman to bring in a plus one.

“Don’t tell your brother I got you in here. I suspect you’re not supposed to be here. Otherwise you would have found your way onto the guest list.”

“Not a word,” she promised.

Nate was right Chuck did not know that his sister was breaking curfew to go to this party. Alex was sure that Chuck would not snitch. He wasn’t the type. But she decided that it would still be best to avoid him. She kept an eye out for him, but she was sure that Chuck was probably busy trying to find a girl to pick up. Alex hated the way her brother treated girls. She was only back in New York for a few months, but she had already noticed that he was not exactly a gentleman when it came to women. Her, his dear little sister, he treated with respect and often even showed his protective side. But she hated seeing how disrespectful he could be towards other girls.

When a waiter offered her a glass of champagne, Alex gratefully took it, even though she wasn’t supposed to drink any alcohol on her meds. But holding the glass gave her something to occupy her hands while she wandered from one room to the next, studying the people around her. There were a lot of people she did not know and she was sure she would not recognize them without their masks either. She had been away for too long.

She spotted Blair, wearing a black ball gown and an elaborate mask. Alex could have recognized Blair anywhere, mask or no mask. It was the way she held herself. Blair’s demeanor was one of confidence and poise. Even when she wasn’t feeling it Blair still managed to look like she was the queen in every situation. Tonight Blair seemed annoyed, she shooed her friends around, and Alex decided not to go talk to her. She wasn’t sure if Blair would even recognized her after almost six years. And as she was an uninvited guest, Alex did not want to cause a scene.

She turned around to walk back into the other room, where people were dancing, and bumped into a girl in a yellow dress.

“I’m so sorry,” the girl said. She seemed in a hurry.

“It’s all right, nothing happened,” Alex said. She noticed that she had spilled some champagne from the glass. Since she did not mean to drink it anyway, she didn’t care much and simply put the glass down on a flower stand next to her.

“Are you okay?” Alex asked the other girl.

“I’m fine, I’m just on my way out.”

“Why leave so early, aren’t you enjoying the party?” Alex asked, smiling.

“Actually I’m having a great time,” the girl said and Alex thought that she could see a glint of mischief in her eyes.

“Why do you want to leave then?”

“I kinda played a prank on this guy,” she confessed. Alex raised an eyebrow, curious to hear more. “He deserved it though! I don’t just run around pranking random people. He was a real asshole to me, and I got my revenge.” The girl smiled confidently as if she was proud of getting her revenge.

“Whoever it was, I’m sure he did deserve it! Guys can be pigs!” Alex laughed, not knowing that the boy in question was her own brother Chuck.

“I should really leave now, I’m not really supposed to be at this party,” the girl confessed again.

“That makes two of us,” Alex said. “I’m Alex by the way.”

“Jenny.”

“It turns out that going to a party uninvited is not as much fun as I thought it would be. I haven’t even danced to a single song yet,” Alex told Jenny. “So how about we dance for one song together before you leave. To make the party worth our while.”

Jenny agreed and they walked together towards the dance floor. A fast pop song was playing and Alex and Jenny began dancing next to each other. Alex took Jenny’s hand and twirled her around. When Jenny came to face Alex again she looked over Alex’s shoulder and Alex saw Jenny’s eyes grow wide in shock underneath her mask.

“Oh no, Blair is coming this way. She can’t see me here!” Jenny said.

Alex was still holding Jenny’s hand. She turned both of them around so that Jenny had her back to Blair now. Alex could see the Queen of the party scanning the room as if she was searching someone.

“I don’t think she’s noticing us. She’s probably looking for someone else,” Alex noted. She and Jenny were standing closer together now, so that she could talk to her in a low voice despite the loud music.

Blair started walking in their direction. Alex was still sure she wasn’t actually walking towards them. But she jokingly said, “Maybe we should do it like in the movies, when they kiss to distract the person coming towards them.”

Alex looked back at Jenny who looked flustered.

“Haha, yeah, maybe we should do that,” Jenny said, and despite her makeup and mask Alex could see her blush.

Jenny turned her head around to see where Blair was now. When she saw that Blair was considerably closer to them then she had thought, she turned back around and placed a kiss on Alex’s lips. Alex was taken by surprise for a moment. She had not thought that Jenny would actually go through with her joke decoy kiss idea. But now that they were kissing Alex gave in to it.

What neither of them knew was that a picture with them kissing in the background would end up on Gossip Girl's blog the very next day.


	3. Unmasked

**Summary for the Chapter:**

> The day after the masked ball Jenny finds out that beneath the mask Alex is not who she thought she was.

**Notes for the Chapter:**

> This is still based on the original idea I had for this story years ago, but I'm not so sure if I still like the one plot detail in this chapter. (More about that in the end notes since I don't want to spoil the chapter.)  
> I wrote this chapter kind of quickly to get it out of the way, so I can get to the good parts of the story. But I am thinking about rewriting it.

“Jenny, hey,” Eric said in surprise when he opened the door. “I wasn’t expecting you.”

“Hi Eric, I hope it’s not an inconvenient time. I just wanted to return this jacket that Serena lent me last night,” Jenny explained.

“It’s fine, I was just surprised to see you. Serena’s not here.”

“Oh well, then I can just give you the jacket.” Jenny said.

“Or you could come in and hang out for a bit,” Eric offered.

“Sure,” Jenny said and followed Eric into the hotel suite.

“I think Serena was just on her way to your place to meet Dan. Or maybe she went to Blair’s,” Eric explained. 

He took Serena’s jacket from Jenny. “I’ll just put this in her room. Why don’t you sit.” He gestured towards the couch.

Jenny sat down, looking around the hotel room. She had never stayed in a hotel suite before. She had only seen luxurious suites like this in movies and she thought there was something glamorous about living like this. It was probably nothing compared to the van der Woodsen apartment that was currently being renovated, Jenny thought.

“So you went to Blair’s ball last night?” Eric asked and sat down on the armchair next to the couch. “Did you have fun?”

“It was amazing! I mean, I wasn’t really supposed to be there, Blair didn’t actually invite me. But I went anyway.” Jenny told Eric all about sneaking into the party and how she had gotten her revenge on Chuck Bass.

“Poor Chuck,” Eric laughed. “But I’m sure he deserved it.”

“Oh yeah, he did,” Jenny said. “I thought the evening was pretty much perfect after that, but then it got even better. I was just about to leave when I ran into this really sweet guy. He asked me to dance and then--”

A knock on the door interrupted Jenny. 

“Just a moment,” Eric said to Jenny and got up to open the door.

“Hey Alex,” he greeted the person at the door.

“Eric! Have you read Gossip Girl’s blog today?” A tall girl with long dark curls brushed past him into the suite

“Come in,” Eric said sarcastically and closed the door.

The girl walked over to the living room area where Jenny was sitting and Jenny thought that she looked eerily familiar.

“Jenny?” the girl said in surprise.

Realization dawned on Jenny. She recognized Alex. Alex, the handsome boy in the tuxedo with whom Jenny had shared a dance and a kiss the previous night. Alex, who wasn’t a boy at all, but a beautiful girl.

“You know each other?” Eric asked.

“We met at Blair’s party last night,” Alex explained.

“The guy I just told you about? That was her,” Jenny added.

Alex looked at Jenny with a grin on her face. “You mistook me for a boy?”

“I’m sorry, I didn’t mean to...” But Jenny didn’t quite know what to say.

“Don’t worry about it. I’m fine with people seeing me either way,” Alex said.

Jenny wasn’t sure what Alex meant by that.

“Anyway you’re not the only one thinking tuxedo equals guy.” 

Alex sat down on the sofa next to Jenny and picked up Eric’s laptop from the coffee table. 

“This is what I came here to show you,” she said to Eric. Alex opened up the Gossip Girl website and there on the front page Jenny saw a picture of herself and Alex kissing.

 

Seen at Blair Waldorf’s Masquerade Ball:

A mysterious prince and a secretive princess dancing. Isn’t that the wonder of masked balls, everybody’s talking about them but no one knows who’s hiding beneath the masks. Do they even belong to the in crowd or did they snuck into an upper east side party without invitation?

Either way, they might have been the cutest couple at the party, since Blair did not get her desired dance with Nate.

 

Both of their faces were obscured by the masks they were wearing. But Jenny of course recognized herself in the picture.

“So you finally got your wish, Gossip Girl noticed you,” Eric joked towards Alex.

“Gossip Girl still doesn’t know I even exist. Wonder of the masked ball indeed,” Alex said. But when she looked up at Jenny she noticed that she did not find this funny at all.

“Don’t worry Jenny. No one’s gonna recognize you in that photo. It’s not even good quality.”

Eric agreed. “If Alex had not told me that’s you, I probably wouldn’t have guessed it,” he reassured her.

“I’m sorry, this is all just a little much at once,” Jenny said. She took the laptop from Alex to have a closer look at the picture. “I only hope Blair won’t figure out that that’s me.”

After scrutinizing herself in the photo for a bit her gaze fell onto the person she was kissing. She noticed how well the tuxedo suited Alex.

“Why the suit?” Jenny asked her.

“It was a masked ball, so I dressed up. I like suits, don’t have much occasion to wear them though. My father doesn’t like me dressing up too androgynous. I wish I wore the same size as my brother, he has an impressive suit collection.”

“You would wear one of Chuck’s suits?” Eric asked.

“Why not? I borrowed a tux from you last night.”

“Wait, Chuck? As in Chuck Bass?” Jenny asked incredulously.

“Yep, that one,” Alex said.

“Chuck Bass is your brother?” Jenny asked again.

“Umm, yeah,” Alex said.

“I had no idea, that he had a sister.”

“Most people don’t.”

Jenny didn’t know what to say. This was all too much at once. 

“I should get going,” Jenny said. “My dad’s probably wondering where I am.”

She quickly grabbed her bag and said her good byes.

Once she had left the suite and walked down the corridor towards the elevator she couldn’t quite decide whether to laugh at this mess or if she should cry. What an idiot she was. Kissing someone she didn’t even know, who turned out to be the sister of Chuck Bass of all people. And to make matters worse end up in a photo on Gossip Girl. She only hoped that Alex wouldn’t find out about the way she had tricked Chuck the previous night into losing all of his clothes and had trapped him on the roof.

* * *

 

“Well that was awkward,” Eric said to Alex after Jenny had left.

“Could have used a warning that the girl I kissed last night was waiting in your apartment for me!”

“I didn’t even know you knew each other. This was just a coincidence.”

“How do you know Jenny anyway?” Alex asked.

“Her brother Dan is dating Serena,” Eric explained. 

Then Alex told him all about the previous night from her perspective and Eric revealed to her that the guy Jenny had executed revenge on had been Chuck.

“Now that explains her weird reaction at his mention. I really hope he didn’t do anything too terrible to her,” Alex said pensively. She had heard some not very nice stories about her brother and the way he treated girls. Alex hoped that Jenny might have been able to truly teach him a lesson. 

But even more than that she hoped that learning that Alex was Chuck’s sister wouldn’t scare Jenny away.

“I think I might really like her,” she told Eric.

**Notes for the Chapter:**

> My original idea for this story, when I thought of it after watching GG for the first time (around 9 years ago), was for Jenny to fall in love with a mysterious boy at the masked ball who later turns out to be a girl and for Jenny to then start questioning her feelings for this girl.   
> But I don't like this idea anymore because I don't want it to seem as if Alex tried to "trick" Jenny in anyway, to make her believe she (Alex) is someone she's not. So there is most likely a rewrite to come. But you still get the general gist of where this story is going.
> 
> I hope you still enjoyed!
> 
> Feel free to give me some feedback especially on the "Jenny mistaking Alex for a boy at the ball" mishap.


End file.
